Glen is a graduate of Huron College, University of Western Ontario with a Bachelor of Arts: Economics. He is an Associate of the Chartered Insurance Institute and has received the designation of Chartered Insurer. More recently he completed the Senior Executive Program at Columbia University. Glen has been employed in the Bermuda insurance market for over twenty years, concentrating on the local market underwriting, and marketing.

Past experience included reinsurance underwriting contract wording, statistical reporting and modeling for property risk, claims management, international market broking and marketing in both the Bermuda and international markets. He is a Past President of the Bermuda Insurance Institute.